The Lovable Reunion - Tom Ricketts on breaking Chicago Cubs curse, World Series rain delay & celebration | Ross & Rizzo

People loved Javy on that team, and I still hear it all the time.

I cried when we traded him, then my son goes, who’d we get, and I say Pete Crow-Armstrong—turns out the kid once slept on our couch during spring break.

All right, I’ve got to nail this intro because you’re too important—Anthony Rizzo still wants to call you Mr. Ricketts, but today it’s Tom; you built a culture and a team that gave Cubs fans an unforgettable moment.

Buying the Cubs was a dream come true for a kid who fell in love with the 1984 team, lived in Wrigleyville bleachers, and even met his wife out there passing beers; I once wrote in my business school app that my dream job was to own a baseball team.

What was that call like to your family when buying the Cubs became real?

My dad first called it the stupidest idea he’d heard, then stood on a rooftop, saw how unique Wrigley and the neighborhood are, and got it; my siblings were all in.

You said from day one you’d rebuild the infrastructure—Mesa, the Dominican, Wrigley—and then you won a title as it all came together.

The old clubhouse was shocking—dirt tunnels and a net to protect a TV by the tee; we fixed it all and added things fans feel, like more bathrooms, exits, and elevators.

Which renovation feels like your baby?

The clubhouse turnaround, hands down; and Mesa is the best in spring training, with my wife’s simple genius note—more shade.

Before every home game I take dated baseballs into the stands to meet fans and hear what’s working; hiding in a suite misses the whole point of Wrigley.

Seeing you in the seats with your kids meant a lot; you also backed my charity when I was twenty‑two, and that support helped us raise close to thirty million dollars.

Your example helped make giving part of our team’s identity, and that momentum carried through 2014 to 2016.

How did you land on Theo Epstein?

I did a secret listening tour with agents, execs, and former players, then met Theo in New York; he led with humility, credited his team, and his track record spoke for itself.

People talk analytics, but Theo’s real edge is people—clear communicator, instantly credible, and he reads the room.

You tore it down and wore the losses—how did you stay the course?

We were honest about prioritizing future wins and told fans it would be brick by brick; trades, drafts, and a lot of small bets stacked up, and by 2014–2015 you could feel it turning.

Theo trading for me after I struggled in San Diego changed my life, and it signaled the plan was real.

The lovable‑loser vibe started fading in 2014 when the team showed fight, then 2015’s Giants series lit the fuse; signing Lester told fans we were serious, and at dinner he asked for another veteran presence—code for David Ross.

I’d just told our agent we needed Ross’s leadership, then Joe arrived, Lester signed, and the belief snowballed.

Joe kept everyone loose and absorbed heat with the media; that tone was critical in a city that can tense up around history.

You and Theo ran end‑of‑year roundtables that killed the ‘that’s how we’ve always done it’ mindset, and the expectation shifted to winning now.

2015 was a massive step, and that Wild Card win in Pittsburgh behind Jake was enormous; 2016 felt wire‑to‑wire inevitable, even with a few late scares.

Players rarely do truly boneheaded things in baseball—most are older and team‑first—but mental mistakes, especially on the bases, drive me nuts.

You were present without pressure—at our weddings, in the seats, and you even flew our families separately during the postseason so the clubhouse stayed ours.

I’m not superstitious, but I won’t jinx it—no parade talk before it’s real.

What was clinching the pennant at Wrigley like?

Lifting that heavy trophy on the field was surreal, and yes, the lip‑readers caught me; Theo and Crane wouldn’t touch it per hockey rules, and I joked we didn’t even have a trophy case yet.

Our playoff routine was rooftop gatherings and endless logistics—tickets, nieces, nephews, and late‑night celebrations.

Down three–one in the World Series—where was your head before Game Five?

I saw the MVP car and thought, not today, but a friend reminded me everyone believes they can win three straight; with Jake set for Game Six, I believed, and Game Five at Wrigley finally exhaled the ballpark.

We flew much of the front office to Cleveland, too—it was all hands together.

Game Seven I kept rotating seats so family could be close; Rajai’s homer had a random fan grabbing me, then the rain sent me up to a suite and it was pure anxiety until the end.

Cleveland’s ownership was gracious, and most fans I met were great.

After we won, I never slept—walked back into the rain‑soaked, peanut‑strewn ballpark at dawn to let it sink in, then flew home to help push a Friday parade on a perfect day.

I’ll never forget a kid on Addison holding a We Did It sign, and then Grant Park—people to the trees in every direction.

People still ask why I stuffed the last‑out ball in my pocket; my agent said someone offered two million, but I handed it to you at Grant Park because that’s where it belonged.

I should’ve pulled a switch with a decoy ball, but I’m glad the real one came home.

We’ve got our reunion in July—what do you carry forward from that year?

I’m a fan first, and I still marvel that 2016 broke our way—if Jason Kipnis straightens that ninth-inning swing, everything changes—so I’m grateful we helped give people those memories. Folks still stop me with Game Seven stories about who they were with, and it reminds me baseball lives in families and friendships.

An older woman once asked if we were going to win another, and I joked we finally got her the one she’d always wanted. That moment captured how we flipped the identity from lovable losers to a team expected to win every year.

People ask if the pressure gets old; sometimes, but the alternative is going back to lovable losers. I’ll take high standards and hold ourselves to them.

You set a vision and delivered, and we were lucky to play small parts. The decade since is packed with the W flags, chalked bricks, and “Grandpa, we did it” notes; after beating St Louis in 2015 you said nobody there would forget it, and that’s how Wrigley feels now—thank you from Rossi and me.

We know it’s rare to sit down with the owner, and you’ve always made us feel like family, so thanks for giving us your time.

Thank you—this was fun.

Alright, that’s a wrap; appreciate the stories and the time.